Dean will always think the best of Sam. It's part of being his older brother. Of course, regardless of how he'd protest, Dean sees the best in most people.

He grows more serious as he watches his baby brother. It's clear something is bothering Sam. He nods, following along, but not sure where Sam is going with this. "Yeah. It was a good move on Jack's part."

It takes Dean a moment to remember who Madison is. "Oh. Werewolf chick you did the horizontal tango with before you killed her," he nods, confident he's caught up. "Give her some time. Some people take longer to adjust." Sam knows this and Dean doesn't get why Sam is so torn up over this. "She want to go back to Purgatory?"